Lexington to early December: the Thriller Parade Oct. 25, the Jack-O-Lantern Trail Oct. 27-30, the Breeders' Cup Oct. 30-31 and Southern Lights from Nov. 27.

Last checked Oct. 24, 2026. This page covers the next six weeks and is retitled at the start of each month. Every event links to its organizer; times and prices are as the organizer published them. City events: LexCall, 311 or 859-425-2255, and the city calendar.

The last week of October is one of Lexington’s busiest of the year. The Halloween and Thriller Parade fills Main Street on Sunday, Oct. 25, and Keeneland, whose fall meet closed Oct. 24, hosts the Breeders’ Cup World Championships on Friday and Saturday, Oct. 30-31. November brings Veterans Day, two Thanksgiving races and the opening of Southern Lights on Nov. 27. For the coming weekend, see things to do this weekend; for theater, concerts and galleries, see arts and exhibitions this month.

What this means for you

  • Breeders’ Cup tickets, parking and shuttles are sold in advance only; nothing is sold at the gate.
  • Allow extra time on Versailles Road (U.S. 60) near Keeneland on Oct. 30 and 31.
  • Daylight saving time ends Sunday, Nov. 1. City offices close for Veterans Day, Wednesday, Nov. 11.

Keeneland and the Breeders’ Cup

The Keeneland Fall Meet closed Saturday, Oct. 24; the spring meet opens April 2, 2027. Dates and tickets are in our Keeneland race meets guide.

Sunrise Trackside: Breeders’ Cup Edition, 7 to 10 a.m. Monday, Oct. 26, through Thursday, Oct. 29, at Keeneland. Watch Breeders’ Cup horses train on the main track. Free, no ticket needed.

Breeders’ Cup World Championships, Friday and Saturday, Oct. 30-31, at Keeneland, the fourth time it has hosted the championships. Admission gates open at 9:30 a.m. Friday and 9 a.m. Saturday. ADA parking is sold out for both days, the Breeders’ Cup says. Gate times, parking prices, shuttles and the bag rules are on our Breeders’ Cup at Keeneland page.

Breeders’ Cup Festival. The citywide festival opens with Purple in the Park, 2 to 5 p.m. Sunday, Oct. 25, at Gatton Park, 795 Manchester St. Free.

Halloween downtown and in the parks

All from the city calendar:

  • Halloween Variety Show and Festival, 4:30 to 6 p.m. Sunday, Oct. 25, Robert F. Stephens Courthouse Plaza, North Limestone. A DJ and Halloween performances by Lexington arts groups. Free.
  • Halloween and Thriller Parade, 6:30 p.m. Sunday, Oct. 25, on Main Street between Quality and Mill streets, followed by the Thriller reenactment from 7 to 8:30 p.m. Food and craft vendors open 4 to 8:30 p.m. Free.
  • Jack-O-Lantern Trail, 6:30 to 10 p.m. Tuesday, Oct. 27, through Friday, Oct. 30, at McConnell Springs Park, 416 Rebmann Lane; gates close at 9:30 p.m. $6 at the gate; children 12 and under free.

Neighborhood community center events, all free:

  • Halloween Dance with Costume Contest, 5 to 7 p.m. Monday, Oct. 26, Kenwick Community Center, 313 Owsley Ave.
  • Hallow-Palooza, 6 to 7:30 p.m. Tuesday, Oct. 27, Castlewood Community Center, 201 Castlewood Drive.
  • Yappy Hour: Howl-o-Ween, 5:30 to 7:30 p.m. Wednesday, Oct. 28, Masterson Station Dog Park, 3051 Leestown Road: a dog costume contest.
  • Fall Halloween Fun Night, 5:30 to 7 p.m. Wednesday, Oct. 28, William Wells Brown Community Center, 548 E. Sixth St.
  • HallowBingo, 5:30 to 7 p.m. Wednesday, Oct. 28, Kenwick Community Center. All ages.
  • All Treats No Tricks, 5 to 7 p.m. Friday, Oct. 30, Kenwick Community Center, 313 Owsley Ave.: a candy giveaway.

More: Halloween events, trick-or-treat hours and fall festivals and pumpkin patches.

Outdoors and nature in November

From the city calendar, all free:

  • Autumn Golden Hour Hike, 4:30 p.m. Friday, Nov. 6, Kelley’s Landing, 8949 Old Richmond Road. About a mile on grass trails along the Kentucky River; register online.
  • Lex Glow Ride, 5 to 7:30 p.m. Saturday, Nov. 7, Coolavin Park, 550 W. Sixth St. A family bike ride in its fifth year, timed for the end of daylight saving time; bring bike lights and reflective gear.
  • Fall Migration Bird Walk, 10:30 a.m. Saturday, Nov. 7, Hisle Farm Park, 3551 Briar Hill Road. Bring binoculars if you have them; some are provided. Register online.
  • Stargazing, 6:30 p.m. Saturday, Nov. 7, Raven Run Nature Sanctuary, 3885 Raven Run Way, with the Bluegrass Amateur Astronomy Club. Weather permitting; call 859-272-6105 that day. No registration.
  • History Walk, 2 p.m. Sunday, Nov. 8, McConnell Springs Park. Registration required; ages 16 and up recommended.
  • Second Friday Bird Walk, 9 a.m. Friday, Nov. 13, Raven Run Nature Sanctuary. About 1.5 to 2 miles; recommended for ages 10 and up.
  • Take a Hike: Treasure Hunt, 10 a.m. Saturday, Nov. 21, Hisle Farm Park. A compass and map scavenger hunt of about a mile; register online.
  • Jr. Naturalist: Native American Games and History, 10 a.m. Saturday, Nov. 28, Raven Run. For grades K-5 with an adult; registration required.
  • Owl Prowl, 5:30 p.m. Wednesday, Dec. 2, Kelley’s Landing. A night hike of about a mile; flashlights and binoculars provided. Register online.

Veterans Day and Thanksgiving

  • Veterans Day, Wednesday, Nov. 11. Lexington-Fayette Urban County Government offices are closed. As of Oct. 24 we found no 2026 Veterans Day parade or ceremony in Lexington posted by its organizer.
  • Turkey Burn and Mini Health Fair, 6 to 8 p.m. Tuesday, Nov. 17, William Wells Brown Community Center, 548 E. Sixth St. Free.
  • The Gobbler Half Marathon, 10K and 5K, 8:30 a.m. Sunday, Nov. 22, Mereworth Farm, 719 Dolan Lane.
  • Lexington Rescue Mission community meal, Wednesday, Nov. 25. Free; time and place not yet posted on the mission’s events page.
  • Thoroughbred Classic 5K, 9 a.m. Thursday, Nov. 26, Keeneland.

Closings and the trash pickup change are on our Thanksgiving page.

Holiday season begins

  • Southern Lights, 5:30 to 10 p.m. nightly from Friday, Nov. 27, at the Kentucky Horse Park, 4089 Iron Works Parkway. $35 a carload. Runs through Dec. 31, closed Christmas Day.
  • Black Friday and Small Business Saturday, Nov. 27 and 28: hours are on our holiday shopping page.
  • Wreath making at Hisle Farm Park, 11 a.m. to 12:30 p.m. Sunday, Nov. 29, 3551 Briar Hill Road. Free.
  • Story Walk, 10 a.m. to 4 p.m. Saturday, Dec. 5, McConnell Springs Park: a self-guided children’s book on the trail. Free.
  • Holiday Nature Ornaments, 1 to 3 p.m. Saturday, Dec. 5, Raven Run Nature Sanctuary. $8; register online.
  • Ashland Illumination, 4 to 7 p.m. Saturday, Dec. 5, Ashland, the Henry Clay Estate, 120 Sycamore Road: the estate’s holiday open house.

The downtown parade and tree lighting are Sunday, Dec. 6: see Christmas parade and tree lighting and holiday lights and Christmas events.

Markets

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Frequently asked questions

What is there to do in Lexington in late October 2026?

The Halloween and Thriller Parade is Sunday, Oct. 25, on Main Street, the Jack-O-Lantern Trail runs Oct. 27-30 at McConnell Springs Park, and the Breeders’ Cup World Championships are at Keeneland Oct. 30-31.

When is the Breeders’ Cup at Keeneland?

Friday and Saturday, Oct. 30-31, 2026. Admission gates open at 9:30 a.m. Friday and 9 a.m. Saturday. Tickets and parking are sold in advance only.

When is the Thriller parade in Lexington in 2026?

Sunday, Oct. 25. The Halloween parade steps off at 6:30 p.m. on Main Street, followed by the Thriller reenactment from 7 to 8:30 p.m. It is free.

When does Southern Lights open in 2026?

Friday, Nov. 27, at the Kentucky Horse Park. It runs nightly 5:30 to 10 p.m. through Dec. 31, closed Christmas Day, at $35 a carload.